• Title/Summary/Keyword: Sesquiterpene

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Anti-inflammatory Effects of $1{\beta}$,$6{\alpha}$-Dihydroxyeudesm-4(15)-ene Isolated from Myrrh on LPS-induced Neuroinflammation in BV2 cells (몰약으로부터 분리된 $1{\beta}$,$6{\alpha}$-dihydroxyeudesm-4(15)-ene의 LPS로 유도된 BV2 미세아교세포에서의 항염증효과)

  • Kim, Dong-Cheol;Yoon, Chi-Su;Ko, Wonmin;Lee, Dong-Sung;Kim, Dae-Sung;Cho, Hyoung-Kwon;Seo, Jungwon;Kim, Sung Yeon;Oh, Hyuncheol;Kim, Youn-Chul
    • Korean Journal of Pharmacognosy
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    • v.46 no.1
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    • pp.12-16
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    • 2015
  • Myrrh is a resinous substance obtained from Commiphora trees, which has long been used as an antiseptic agent. A sesquiterpene, $1{\beta}$, $6{\alpha}$-dihydroxyeudesm-4(15)-ene (DE), was isolated from the hot water extract of Myrrh. In the present study, we found that DE attenuates the lipopolysaccharide (LPS)-induced inflammation in BV2 microglial cells. DE significantly inhibited LPS-induced production of pro-inflammatory mediators such as nitric oxide (NO) and prostaglandin $E_2$ ($PGE_2$) in BV2 microglia in a concentration-dependent manner without cytotoxic effect. Furthermore, DE dose-dependently suppressed the protein expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). These results suggest that DE may be a good candidate to regulate LPS-induced inflammatory response.

An Identification of Volatile Terpenes in Allelopathic Weeds (Allelopathy 작용성(作用性)을 나타내는 잡초(雜草)중의 휘발성(揮發性) Terpene류(類)의 동정(同定))

  • Chun, J.C.;Han, K.W.
    • Korean Journal of Weed Science
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    • v.9 no.2
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    • pp.149-153
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    • 1989
  • Volatile terpenes responsible for allelopathic activity in four weed species were identified using gas chromatography (GC) and GC-mass spectrometry. Artemisia asiatica Nakai contained 26 volatile terpenes, consisting of 16 monoterpenes and 10 sesquiterpenes, whereas there were only four terpenes in Trifolium repens L. and three terpenes each in Portulaca oleracea L. and Capsella bursa-pastoris (L,) Medik. Suspected allelochemics were ${\alpha}$-phellandrene, 1,8-cineole, limonene, ${\alpha}$-pinene, borneol, selinene, and caryophyllene in A. asiatica, ${\alpha}$-pinene and ${\beta}$-caryophyllene in T. repens, and ${\alpha}$-pinene in C. bursapastoris. No these compounds were found in P. oleracea.

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Essential Oil Content and Composition of Aromatic Constituents in Leaf of Saururus chinensis, Angelica dahurica and Cnidium officinale (삼백초, 구릿대, 천궁의 잎 향기성분 조성과 정유함량)

  • Kim, Sang-Kuk;Kim, Young-Hyo;Kang, Dong-Kyoon;Chung, Sang-Hwan;Lee, Seong-Phil;Lee, Sang-Chul
    • Korean Journal of Medicinal Crop Science
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    • v.6 no.4
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    • pp.299-304
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    • 1998
  • This experiment was conducted to determine the essential oil content and the aromatic constituents in the leaves of Saururus chinensis Baill, Angelica dahurica Fischer and Cnidium officinale Makino. Volatile aromatic compounds in three aromatic medicinal plants were extracted with steam distillation extraction method and identified by GC/MS. Major aromatic compounds in Saururus chinensis Baill were 1,6-octadien-3-ol, 1, 3-benzodioxole, myristicin, ${\alpha}-cadinol$ and patchouene. Major aromatic compounds in Angelica dahurica Fischer were terpinolene, 3-carene, ${\beta}-caryophyllene$, ${\beta}-cubebene$, butylated hydroxy toluene, caryophyllene oxide, piperonal, and in Cnidium officinale Makino were aristolene, benzocycloheptene, ylangene, valencene, ${\beta}-cedrene$, satene, and menthofuran. Essential oil content was highest in Saururus chinensis plant.

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Analyses of the Volatile Flavor Composition of Essential Oils from Chrysanthemum zawadskii var. latilobum Kitamura and Aster yomena Makino (구절초와 쑥부쟁이 정유의 휘발성 향기성분 분석)

  • Choi, Hyang-Sook
    • The Korean Journal of Food And Nutrition
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    • v.31 no.3
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    • pp.378-387
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    • 2018
  • This study investigated the volatile flavor composition of essential oils from Chrysanthemum zawadskii var. latilobum Kitamura and Aster yomena Makino. The essential oils obtained by the hydrodistillation extraction method from the aerial parts of the plants were analyzed by gas chromatography (GC) and GC-mass spectrometry (GC-MS). One hundred (95.04%) volatile flavor compounds were identified in the essential oil from the C. zawadskii var. latilobum Kitamura. The major compounds were valencene (10.82%), ${\delta}$-cadinol (9.77%), hexadecanoic acid (8.70%), 2-methyl-4-(2,6,6-trimethylcyclohex-1-enyl) but-2-en-1-ol (3.67%), and 2-(2,4-hexadiynylidene)-1,6-dioxaspiro[4,4]non-3-ene (3.57%). Ninety-eight (93.83%) volatile flavor compounds were identified in the essential oil from the Aster yomena Makino. The major compounds were and 3-eicosyne (13.61%), 9,10,12-octadecatrienoic acid (7.8%), ${\alpha}$-caryophyllene alcohol (6.83%), 9-octadecynoic acid (6.03%), and ${\alpha}$-caryophyllene (5.74%). Although the two plants are apparently very similar, the chemical composition of the essential oils was significantly different in quality and quantity. In the case of C. zawadskii var. latilobum Kitamura, the sesquiterpene, valencene was found to be 10.82%, but it was not identified in A. yomena Makino. ${\delta}$-Cadinol appeared higher in C. zawadskii var. latilobum Kitamura than in A. yomena Makino. A clear characteristic of A. yomena Makino essential oil is that it has a high content of caryophyllene derivatives. The ${\alpha}$-caryophyllene alcohol contained in A. yomena Makino was relatively high at 6.83%, although the compound was not identified in C. zawadskii var. latilobum Kitamura. Also ${\alpha}$-caryophyllene was shown to be higher in A. yomena Makino than in C. zawadskii var. latilobum Kitamura.

Alkaloids of Linderae Radix suppressed the lipopolysaccharide-induced expression of cytokines in cultured macrophage RAW 264.7 cells

  • Chou, David Jiyao;Lam, Kelly Yinching;Chen, Jianping;Yao, Ping;Dong, Tina Tingxia;Xiong, Aizhen;Chou, Guixin;Wang, Zhengtao;Tsim, Karl Wah-Keung
    • CELLMED
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    • v.4 no.4
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    • pp.28.1-28.27
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    • 2014
  • Linderae Radix, the dry roots of Lindera aggregata (Sims) Kosterm, has long been used as traditional Chinese medicine for treatment of inflammatory diseases. The total alkaloids are believed to be the active components responsible for anti-inflammation of Linderae Radix. Here, the total alkaloids of Linderae Radix were extracted and isolated, including 12 isoquinoline alkaloids and 1 furan sesquiterpene. Within the alkaloids, norisoboldine, boldine, linderaline, isoboldine, reticuline, N-methyllaurotetanine, norjuziphine were found to be the major ingredients. In lipopolysaccharide-treated macrophage RAW 264.7 cells, application of Linderae Radix extract, or total alkaloids, suppressed the transcription of proinflammatory cytokines, interleukin-$1{\beta}$ and interleukin-6. Out of the 12 alkaloids, norisoboldine, boldine, and isoboldine were tested in lipopolysaccharide-treated macrophages, and norisoboldine was the strongest alkaloid in suppressing the cytokine expressions. The current studies suggested that the identification of alkaloids from Linderae Radix could provide a plausible explanation for herbal therapeutic functions.

A Curcuminoid and Two Sesquiterpenoids from Curcuma zedoaria as Inhibitors of Nitric Oxide Synthesis in Activated Macrophages

  • Jang, Mi-Kyung;Lee, Hwa-Jin;Kim, Ji-Sun;Ryu , Jae-Ha
    • Archives of Pharmacal Research
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    • v.27 no.12
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    • pp.1220-1225
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    • 2004
  • The overproduction of nitric oxide (NO) by inducible nitric oxide synthase (iNOS) is known to be responsible for vasodilation and hypotension observed in septic shock and inflammation. Inhibitors of iNOS, thus, may be useful candidates for the treatment of inflammatory diseases accompanied by overproduction of NO. In the course of screening oriental anti-inflammatory herbs for the inhibitory activity of NO synthesis, a crude methanolic extract of Curcuma zedoaria exhibited significant activity. The activity-guided fractionation and repetitive chromatographic procedures with the EtOAc soluble fraction allowed us to isolate three active compounds. They were identified as 1,7-bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one (1), procurcumenol (2) and epiprocurcumenol (3) by spectral data analyses. Their concentrations for the 50% inhibition of NO production $(IC_{50})$ in lipopolysaccharide (LPS)-activated macrophages were 8, 75, 77 ${\mu}M$, respectively. Compound 1 showed the most potent inhibitory activity for NO production in LPS-activated macrophages, while the epimeric isomers, compound 2 and 3 showed weak and similar potency. Inhibition of NO synthesis by compound 1 was very weak when activated macrophages were treated with 1 after iNOS induction. In the immunoblot analysis, compound 1 suppressed the expression of iNOS in a dose-dependent manner. In summary, 1,7-bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one from Curcuma zedoaria inhibited NO production in LPS-activated macrophages through suppression of iNOS expression. These results imply that the traditional use of C. zedoaria rhizome as anti-inflammatory drug may be explained at least in part, by inhibition of NO production.

Chemical Constituents from the Aerial Parts of Vernonia cinerea L. and Their Anti-Inflammatory Activity (베르노니아 시네레아 지상부의 화학 성분 및 항염증 활성)

  • Youn, Ui Joung;Chang, Leng Chee
    • Korean Journal of Medicinal Crop Science
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    • v.24 no.6
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    • pp.437-443
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    • 2016
  • Background: Previous phytochemical studies of whole Vernonia cinerea L. plants have identified sesquiterpene lactones, sterols, and triterpenes, which possess anticancer, antifeedant, and antimalarial activities. However, there are no reports of other types of bioactive metabolites. Therefore, the present study aimed to identify phenolic compounds with anti-inflammatory activity in the aerial parts of the plant. Methods and Results: Compounds were isolated from the aerial parts of V. cinerea using a silica and C-18 gel columns and semi-preparative HPLC instrument, and the structures of the compounds were determined using one- and two- dimension nuclear magnetic resonance spectroscopy and mass spectroscopy. The chloroform soluble extracts and isolated compounds were evaluated for their anti-inflammatory potential based on their ability to inhibit nitric oxide production and $TNF-{\alpha}$ induced $NF-{\kappa}B$ activity. Conclusions: Phytochemical study of the aerial parts of V. cinerea led to the isolation of six phenolic compounds. Compound 1 was a major metabolite, and to the best of our knowledge, compounds 2 - 6 were isolated from V.cinerea for the first time. Among the isolates, compounds 1 and 3 exhibited $TNF-{\alpha}$-induced $NF-{\kappa}B$ activity with $IC_{50}$ values of 7.5 and 11.5 M, respectively, and the inhibitory activity of phenyl propanoid compound 3 on $TNF-{\alpha}$-induced $NF-{\kappa}B$ was evaluated for the first time.

Chemical Composition and Biological Activity of Essential Oil of Agastache rugosa (Fisch. & C. A. Mey.) O. Kuntze (배초향 에센셜오일의 화학적 조성과 생리활성 특성)

  • Hong, Min Ji;Kim, Ju Ho;Kim, Hee Yeon;Kim, Min Ju;Kim, Song Mun
    • Korean Journal of Medicinal Crop Science
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    • v.28 no.2
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    • pp.95-110
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    • 2020
  • Background: In Korea, Agastache rugosa (Fisch. & C. A. Mey.) O. Kuntze is one of the well-known perennial plants belonging to Lamiaceae. This mint-fragranced plant has long been used for the treatment of abdominal pain, congestion, chills, and diarrhea since the Goryeo Dynasty. Although this plant has various medicinal properties, it is only used as a spice and for landscape purposes. Methods and Results: The objective of this paper was to review the chemical composition and biological properties of the essential oil of A. rugosa. Several studies reported that the essential oil contains more than 60 different chemical components of monoterpene and sesquiterpene hydrocarbons and oxygenated hydrocarbons. The major component is methyl chavicol (estragole), accounting for 64% - 88% of the oil. The chemical composition of this essential oil vaired widely according to the planting time, environmental conditions, planting distance, fertilizer application, and harvesting time. Conclusions: The essential oil of A. rugosa possesses various pharmacological properties such as antioxidant, antibacterial, anticancer, antiviral, nematicidal, antifungal, insecticidal, wrinkle improver, stress reliever, and Alzheimer's disease alleviator. Hence, the essential oil from A. rugosa could be used for the development of high value-added industrial products in the near future.

Butyrylcholinesterase Inhibitory Guaianolides from Amberboa ramosa

  • Khan Sher Bahadar;Haq Azhar-ul;Perveen Shagufta;Afza Nighat;Malik Abdul;Nawaz Sarfraz Ahmad;Shah Muhammad Raza;Choudhary Muhammad lqbal
    • Archives of Pharmacal Research
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    • v.28 no.2
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    • pp.172-176
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    • 2005
  • Phytochemical investigation of the whole plant of Amberboa ramosa led to the isolation of six sesquiterpene lactones which could be identified as $8{\alpha}$-hydroxy-$11{\beta}$-methyl-$1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H,\;11{\alpha}H-guai-10(14)$, 4(15)-dien-6, 12-olide(2), $3{\beta},\;8{\alpha}-dihydroxy-11{\alpha}-methyl-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H,\;11{\beta}H-guai-10(14)$, 4(15)-dien-6, 12-olide (2), $3{\beta},\;4{\alpha},\;8{\alpha}-trihydroxy-4{\beta}(hydroxymethyl)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide (3), $3{\beta},\;4{\alpha},\;8{\alpha}-trihydroxy-4{\beta}-(chloromethyl)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide(4), $3{\beta},\;4{\alpha},\;dihydroxy-4{\beta}-(hydroxymethyl)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide(5), $3{\beta},\;4{\alpha}-dihydroxy-4{\beta}-(chloromethyl)-8{\alpha}-(4-hydroxymethacrylate)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide (6) by spectroscopic methods. All of them showed inhibitory potential against butyrylcholinesterase.

Relationship Between Biological Activity and Structure of Alantolactone (Alantolactone의 구조와 생물학적 활성)

  • 권영명
    • Journal of Plant Biology
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    • v.17 no.2
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    • pp.69-83
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    • 1974
  • To elucidate the relationship between chemical structure and biological activity of alantolactone, and also to investigate the relationship between the growth of cells and the respiration of Chlorella pyrenoidosa affected by alantolactone, alantolactone and isoalantolactone were isolated from Inula helenium L., and di-, and tetrahydroalantolactones were prepared by the hydrogenation. At a concentration of 5$\times$10-5M alantolactone, the growth rate of Chlorella was greatly reduced. The viability of cells was also reduced over 50% within 2 hr at a concentration of 2.5$\times$10-4M alantolactone. However, oxygen uptake was increased by 20% over 3 hr. And 14CO2 production from glucose-1-14C, glucose-6-14C and 14C-acetate-U.L. was also increased by alantolactone. Biological activityof alantolactone was significantly reduced by cysteine, reduced glutathione or cystine but not by tryptophan or histidine. It was detected by spectrophotometrically and by TLC that alantolactone was also reacted with thiols except cystine. The solution of alantolactone reached with thiol gave the UV absorption spectrum of $\alpha$-saturated ${\gamma}$-lactone, and most of SH groups were disappeared by the addition reaction. From the reaction mixture of alantolactone and cysteine, a lactone adduct was isolated and purified. Isoalantolactone had shown similar activity as alantolactone, however, it was appeared that di-, and tetrahydroalantolactones were not only inactive biologically but also in vitro. It was concluded that there was no correlationship between increased respiration rate and mortality of Chlorella. During the respiration TCA cycle was activated, however it was uncertain that the activation of EMP or HMP was also appeared. Alantolactone and isoalantolactone were biologically active compounds but others were inactive. The reactivity of $\alpha$-methylene ${\gamma}$-lactone moiety toward SH group was principally responsible for its biological activity in sesquiterpene lactones.

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